US5487770A - Detection of marked mineral oils and novel azo dyes - Google Patents

Detection of marked mineral oils and novel azo dyes Download PDF

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Publication number
US5487770A
US5487770A US08/321,629 US32162994A US5487770A US 5487770 A US5487770 A US 5487770A US 32162994 A US32162994 A US 32162994A US 5487770 A US5487770 A US 5487770A
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hydrogen
alkyl
strongly
yellow
ppm
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Rainer Dyllick-Brenzinger
Friedrich-Wilhelm Raulfs
Ulrike Schlosser
Karin H. Beck
Gerhard Scholz
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BASF SE
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BASF SE
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Assigned to BASF AKTIENGESELLSCHAFT reassignment BASF AKTIENGESELLSCHAFT ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BECK, KARIN HEIDRUN, DYLLICK-BRENZINGER, RAINER, RAULFS, FRIEDRICH-WILHELM, SCHLOSSER, ULRIKE, SCHOLZ, GERHARD
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
    • C09B29/12—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group of the benzene series
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/24—Monoazo dyes prepared by diazotising and coupling from coupling components containing both hydroxyl and amino directing groups
    • C09B29/26—Amino phenols
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
    • C09B31/02—Disazo dyes
    • C09B31/06—Disazo dyes from a coupling component "C" containing a directive hydroxyl group
    • C09B31/062—Phenols
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/003—Marking, e.g. coloration by addition of pigments
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/226—Organic compounds containing nitrogen containing at least one nitrogen-to-nitrogen bond, e.g. azo compounds, azides, hydrazines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
    • C10M171/007—Coloured or dyes-containing lubricant compositions
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N31/00—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods
    • G01N31/22—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods using chemical indicators
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/26—Oils; Viscous liquids; Paints; Inks
    • G01N33/28—Oils, i.e. hydrocarbon liquids
    • G01N33/2835—Specific substances contained in the oils or fuels
    • G01N33/2882—Markers

Definitions

  • the present invention relates to a novel method for detecting azo dye marked mineral oils, the use of monoazo or disazo dyes as markers for mineral oils, and novel azo dyes.
  • U.S. Pat. No. 5,156,653 discloses the use of phenylazophenols for marking mineral oils.
  • the markers are detected there by shaking the marked mineral oil with a mixture of water, diethylene glycol and methoxyethoxypropylamine to form a mineral oil phase and an aqueous phase containing the azo dye.
  • the method of detection described there is not satisfactory. It does not have universal utility and frequently produces only an extremely weak coloring of the aqueous phase, since some of the dye used remains in the oil phase.
  • this object is achieved by a method for detecting azo dye marked mineral oils by treating the marked mineral oil with an extractant comprising water, a solvent and a base, the azo dye transferring from the mineral oil into the aqueous phase, which comprises using as marker an azo dye of the formula I ##STR2## where ring A may be benzofused,
  • n 1 to 4
  • X 1 is hydrogen, C 1 -C 4 -alkyl, cyano or nitro
  • X 2 is hydrogen, C 1 -C 4 -alkyl, cyano, nitro, C 1 -C 4 -alkoxy or C 1 -C 16 -alkoxycarbonyl,
  • X 3 is hydrogen, C 1 -C 4 -alkyl, cyano or C 1 -C 16 -alkoxycarbonyl, and
  • X 4 is hydrogen, hydroxyl, C 1 -C 8 -alkyl, which may be phenyl-substituted, C 1 -C 4 -alkoxy, amino, C 1 -C 4 -dialkylamino or C 1 -C 16 -monoalkylamino whose alkyl chain may be interrupted by from 1 to 3 oxygen atoms in the ether function,
  • R 1 , R 2 , R 3 and R 4 are each independently of the others C 1 -C 16 -alkyl or benzyl.
  • Any alkyl appearing in the abovementioned formulae may be straight-chain or branched.
  • X 1 , X 2 , X 3 , X 4 , R 1 , R 2 , R 3 and R 4 are each for example methyl, ethyl, propyl, isopropyl, butyl, isobutyl or sec-butyl.
  • X 4 , R 1 , R 2 , R 3 and R 4 may each also be for example pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, 2-methylpentyl, heptyl, octyl, 2-ethylhexyl or isooctyl.
  • R 1 , R 2 , R 3 and R 4 may each also be for example nonyl, isononyl, decyl, isodecyl, undecyl, dodecyl, tridecyl, 3,5,5,7-tetramethylnonyl, isotridecyl, tetradecyl, pentadecyl or hexadecyl (the above designations isooctyl, isononyl, isodecyl and isotridecyl are trivial names derived from the oxo process alcohols - cf. Ullmanns Encyclopadie der ischen Chemie, 4th edition, Volume 7, pages 215 to 217, and Volume 11, pages 435 and 436).
  • X 4 may also be for example dimethylamino, diethylamino, dipropylamino, diisopropylamino, dibutylamino, methylamino, ethylamino, propylamino, isopropylamino, butylamino, isobutylamino, sec-butylamino, pentylamino, isopentylamino, neopentylamino, tert-pentylamino, hexylamino, 2-methylpentylamino, heptylamino, octylamino, 2-ethylhexylamino, isooctylamino, nonylamino, isononylamino, decylamino, isodecylamino, undecylamino, dodecylamino, tridecylamino, 3,5,5,7-tetramethylnonylamino
  • X 2 and X 4 may each also be for example methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy or sec-butoxy.
  • X 2 and X 3 may each also be for example methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, pentyloxycarbonyl, isopentyloxycarbonyl, neopentyloxycarbonyl, tert-pentyloxycarbonyl, hexyloxycarbonyl 2-methylpentyloxycarbonyl, heptyloxycarbonyl, octyloxycarbonyl, 2-ethylhexyloxycarbonyl, isooctyloxycarbonyl, nonyloxycarbonyl, isononyloxycarbonyl, decyloxycarbonyl, isodecyloxycarbonyl, undecyloxycarbonyl, dodecyloxycarbonyl, tridecyloxycarbonyl, isotridecyloxycarbonyl,
  • X 1 is hydrogen or C 1 -C 4 -alkyl
  • X 2 is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or C 1 -C 16 -alkoxycarbonyl,
  • X 3 is hydrogen, C 1 -C 4 -alkyl, or C 1 - 16 -alkoxycarbonyl, and
  • n, Y and X 4 are each as defined above.
  • X 1 is hydrogen, cyano or nitro
  • X 2 is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or C 1 -C 13 -alkoxycarbonyl,
  • X 3 is hydrogen or C 1 -C 4 -alkyl
  • X 4 is hydrogen or C 1 -C 4 -alkyl, which may be phenyl-substituted.
  • X 2 is hydrogen
  • X 3 is hydrogen or C 1 -C 4 -alkyl
  • X 4 is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -dialkylamino or C 1 -C 16 -monoalkylamino,
  • X 5 is hydrogen or C 1 -C 4 -alkyl
  • X 6 is hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy
  • X 1 , X 2 and X 3 are different from hydrogen
  • X 2 may also be cyano when X 4 is C 1 -C 4 -dialkylamino
  • X 2 may also be C 1 -C 4 -alkoxycarbonyl when all the radicals X 4 , X 5 and X 6 are different from hydrogen
  • one of the radicals X 1 , X 2 or X 3 may also be nitro when X 4 is C 1 -C 16 -monoalkylamino and X 6 is C 1 -C 4 -alkyl.
  • azo dyes of the formula Ia where X 1 is hydrogen, X 2 is methyl or C 1 -C 13 -alkoxycarbonyl, and X 3 is hydrogen or methyl.
  • Suitable alkali or alkaline earth metal hydroxides or alkali metal carbonates for use in the method of the invention include for example lithium hydroxide, sodium hydroxide, potassium hydroxide, magnesium hydroxide, calcium hydroxide, lithium carbonate, sodium carbonate and potassium carbonate.
  • Suitable ammonium compounds include for example tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, benzyltrimethylammonium hydroxide, benzyltriethylammonium hydroxide and benzyltributylammonium hydroxide.
  • alkali or alkaline earth metal hydroxides as base is preferred with particular attention being drawn to alkali metal hydroxides.
  • lithium hydroxide sodium hydroxide or potassium hydroxide as base
  • sodium hydroxide being of particular importance.
  • the alkali or alkaline earth metal hydroxides, alkali metal carbonates or ammonium compounds are preferably used directly in the form of an aqueous solution, this aqueous solution generally having an alkali or alkaline earth metal hydroxide, alkali metal carbonate or ammonium compound content from 0.1 to 10% by weight, preferably from 1 to 10% by weight, each percentage being based on the weight of the aqueous solution.
  • Suitable solvents are partially or completely water-miscible organic solvents.
  • Preferred solvents are 1-methylpyrazole, pyrrolidin-2-one, 1-methylpyrrolidin-2-one, dimethyl sulfoxide and sulfolane.
  • the extractant can also be of advantage for the extractant to include further admixtures, for example 4-nonylphenol, or for the mineral oil to have 4-nonylphenol added to it prior to the extraction.
  • the proportion of solvent typically ranges from 50 to 99% by weight, preferably from 90 to 99% by weight.
  • Suitable solvents include preferably aromatic hydrocarbons, such as toluene, xylene, dodecylbenzene, diisopropylnaphthalene or a mixture of higher aromatics commercially available from Shell as Shellsol® AB.
  • the solubility may be improved in a conventional manner by using further, co-solvents, for example alcohols, such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, pentanol, hexanol, heptanol, octanol, 2-ethylhexanol or cyclohexanol, glycols, such as butylethylene glycol or methylpropylene glycol, amines, such as triethylamine, diisooctylamine, dicyclohexylamine, aniline, N-methylaniline, N,N-dimethylaniline, toluidine or xylidine, alkanolamines, such as 3-(2-methoxyethoxy)propylamine, o-cresol, m-cresol, p-cresol, ketones, such as diethyl ketone or cyclohexanone,
  • the azo dye of the formula I transfers into the aqueous phase, which takes on a distinctly visible color in the process.
  • the method of the invention provides a very simple means of detecting mineral oils marked with azo dyes of the formula I.
  • a further advantage of the method of the invention is that it permits the extraction of dyes which have only little acidity.
  • the present invention further provides for the use of azo dyes of the abovementioned formulae Ia and Ib for marking mineral oils.
  • Preference for marking mineral oils is further given to the use of azo dyes of the formula Ia where X 1 is hydrogen, X 2 is methyl or C 1 -C 13 -alkoxycarbonyl, and X 3 is hydrogen or methyl.
  • Mineral oils for the purposes of the present invention include for example motor fuels, such as gasoline, kerosine or diesel fuel, or oils, such as fuel oil or engine oil.
  • the azo dyes of the formula Ia or Ib are especially suitable for marking mineral oils where a form of identification is required, for example for tax reasons. To keep the costs for this to a minimum, it is desirable to keep the amount of marker used to a minimum.
  • Marking for the purposes of the present invention is the addition of the azo dyes of the formula Ia or Ib to mineral oils in such a concentration that, to the human eye, the mineral oils have barely any or no visible color, although the dyes of the formulae Ia and Ib are readily and distinctly visibly detectable by the methods of detection more particularly described herein.
  • the azo dyes of the formula Ia or Ib are used either without a solvent or in the form of solutions.
  • the azo dyes of the formula Ia or Ib to be used according to the invention have the advantage of being suitable, depending on their concentration, of conferring a clearly visible color on mineral oils and/or for use as marker substances.
  • the azo dyes of the formula Ia or Ib to be used according to the invention permit very simple detection of marked mineral oils, even if the marker substances are present only in a concentration of about 10 ppm or less.
  • the azo dyes of the formula Ia have the application advantage of very good solubility and also excellent dilutability. Moreover, in the detection reaction, they give distinctly more bathochromic hues than the dyes known from U.S. Pat. No. 5,156,653.
  • Y 2 is hydrogen
  • Y 3 is hydrogen or C 1 -C 4 -alkyl
  • X 4 is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -dialkylamino or C 1 -C 16 -monoalkylamino,
  • X 5 is hydrogen or C 1 -C 4 -alkyl
  • X 6 is hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy
  • Y 2 may also be cyano when X 4 is C 1 -C 4 -dialkylamino, c) Y 2 may also be C 1 -C 4 -alkoxycarbonyl when all the radicals X 4 , X 5 and X 6 are different from hydrogen, and d) one of the radicals Y 1 , Y 2 or Y 3 or may also be nitro when X 4 is C 1 -C 16 -monoalkylamino and X 6 is C 1 -C 4 -alkyl.
  • novel azo dyes of the formula II are obtainable in a conventional manner, for example by diazotizing an aniline of the formula III ##STR8## where Y 1 , Y 2 and Y 3 are each as defined above, and coupling the resulting diazonium compound with a phenol of the formula IV ##STR9## where X 4 , X 5 and X 6 are each as defined above.
  • the further azo dyes of the formula I and those of the formula Ia are generally compounds known per se. They are described for example in U.S. Pat. No. 5,156,653 or U.S. Pat. No. 4,473,376 or can be obtained by the methods mentioned therein.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
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  • Immunology (AREA)
  • Pathology (AREA)
  • Physics & Mathematics (AREA)
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  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Food Science & Technology (AREA)
  • Medicinal Chemistry (AREA)
  • Biophysics (AREA)
  • Molecular Biology (AREA)
  • Lubricants (AREA)
  • Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Paints Or Removers (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Investigating Or Analysing Materials By Optical Means (AREA)
  • Cosmetics (AREA)
  • Lubrication Of Internal Combustion Engines (AREA)
  • Coloring (AREA)
  • Spectrometry And Color Measurement (AREA)
  • Developing Agents For Electrophotography (AREA)
  • Analysing Materials By The Use Of Radiation (AREA)
  • Plural Heterocyclic Compounds (AREA)
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US08/321,629 1993-10-12 1994-10-12 Detection of marked mineral oils and novel azo dyes Expired - Fee Related US5487770A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4334678A DE4334678A1 (de) 1993-10-12 1993-10-12 Verfahren zum Nachweis von markierten Mineralölen sowie neue Azofarbstoffe
DE4334678.2 1993-10-12

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US5487770A true US5487770A (en) 1996-01-30

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US (1) US5487770A (no)
EP (1) EP0723574B1 (no)
JP (1) JPH09504314A (no)
KR (1) KR100300774B1 (no)
CN (1) CN1046756C (no)
AT (1) ATE180823T1 (no)
AU (1) AU682540B2 (no)
BR (1) BR9407810A (no)
CA (1) CA2172959A1 (no)
CZ (1) CZ9601018A3 (no)
DE (2) DE4334678A1 (no)
DK (1) DK0723574T3 (no)
ES (1) ES2134357T3 (no)
FI (1) FI961602A (no)
GR (1) GR3030494T3 (no)
HU (1) HU217768B (no)
MX (1) MX193901B (no)
NO (1) NO961434D0 (no)
PH (1) PH32006A (no)
PL (1) PL313967A1 (no)
TW (1) TW291494B (no)
WO (1) WO1995010581A1 (no)
ZA (1) ZA947908B (no)

Cited By (10)

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US5672182A (en) * 1995-04-13 1997-09-30 United Color Manufacturing Inc. Developer system for base reactable petroleum fuel markers
US5737871A (en) * 1996-04-26 1998-04-14 Morton International, Inc. Method of preparing and utilizing petroleum fuel markers
EP1010978A1 (fr) * 1998-12-16 2000-06-21 Total Raffinage Distribution S.A. Indicateur coloré pour la mesure de la répartition des familles d'hydrocarbures
US6482651B1 (en) 1999-06-30 2002-11-19 United Color Manufacturing, Inc. Aromatic esters for marking or tagging petroleum products
US6514917B1 (en) * 2001-08-28 2003-02-04 United Color Manufacturing, Inc. Molecular tags for organic solvent systems
US20030191186A1 (en) * 2000-08-29 2003-10-09 Ekwuribe Nnochiri Nkem Immunoregulatory compounds and derivatives and methods of treating diseases therewith
US20070060552A1 (en) * 2001-08-29 2007-03-15 Ekwuribe Nnochiri N Methods and compositions employing 4-aminophenylacetic acid compounds
US20080033153A1 (en) * 2004-07-07 2008-02-07 Riggs-Sauthier Jennifer A Synthesis of Azo Bonded Immunoregulatory Compounds
US20080277606A1 (en) * 2005-11-11 2008-11-13 Molecular Vision Limited Microfluidic Device
WO2009120563A1 (en) * 2008-03-25 2009-10-01 The Lubrizol Corporation Marker dyes for petroleum products

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BR9604958A (pt) * 1995-04-13 1998-07-14 United Color Mfg Inc Indicadores de petróleo incolores
GB0222728D0 (en) * 2002-10-01 2002-11-06 Shell Int Research System for identifying lubricating oils
GB0406770D0 (en) * 2004-03-25 2004-04-28 Customs & Excise Hydrocarbon markers
CN106893356A (zh) * 2017-01-10 2017-06-27 泉州市希姆色彩研究院有限公司 一种高水牢度的分散橙染料及其制备方法
WO2022161960A1 (en) 2021-01-29 2022-08-04 Basf Se A method of marking fuels
US20240219366A1 (en) 2021-04-20 2024-07-04 Basf Se A method of detecting one or more markers in a petroleum fuel using a photoacoustic detector

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US2925333A (en) * 1955-05-24 1960-02-16 Eastman Kodak Co Colored hydrocarbons
US3704106A (en) * 1967-10-24 1972-11-28 Morton Int Inc Colored petroleum distillate
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EP1010978A1 (fr) * 1998-12-16 2000-06-21 Total Raffinage Distribution S.A. Indicateur coloré pour la mesure de la répartition des familles d'hydrocarbures
FR2787577A1 (fr) * 1998-12-16 2000-06-23 Total Raffinage Distribution Indicateur colore pour la mesure de la repartition des familles d'hydrocarbures contenues dans un melange, son procede d'obtention et ses utilisations
US6451615B1 (en) 1998-12-16 2002-09-17 Total Raffinage Distribution S. A. Colored indicator to measure the distribution of the hydrocarbon families contained in a mixture, the procedure for obtaining it, and its uses
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US7151095B2 (en) 2000-08-29 2006-12-19 Nobex Corporation Immunoregulatory compounds and derivatives and methods of treating diseases therewith
US7425578B2 (en) 2000-08-29 2008-09-16 Biocon Limited Immunoregulatory compounds and derivatives and methods of treating diseases therewith
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US7119119B2 (en) 2000-08-29 2006-10-10 Biocon Limited Immunoregulatory compounds and derivatives and methods of treating diseases therewith
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US20030191186A1 (en) * 2000-08-29 2003-10-09 Ekwuribe Nnochiri Nkem Immunoregulatory compounds and derivatives and methods of treating diseases therewith
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US7932366B2 (en) 2004-07-07 2011-04-26 Biocon Limited Synthesis of azo bonded immunoregulatory compounds
US8314214B2 (en) 2004-07-07 2012-11-20 Biocon Limited Synthesis of azo bonded immunoregulatory compounds
US8754197B2 (en) 2004-07-07 2014-06-17 Biocon Limited Synthesis of azo bonded immunoregulatory compounds
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DK0723574T3 (da) 1999-11-15
HU217768B (hu) 2000-04-28
KR960705003A (ko) 1996-10-09
CN1046756C (zh) 1999-11-24
ZA947908B (en) 1996-04-11
CA2172959A1 (en) 1995-04-20
GR3030494T3 (en) 1999-10-29
MX193901B (no) 1999-11-01
FI961602A0 (fi) 1996-04-11
NO961434L (no) 1996-04-11
AU7784294A (en) 1995-05-04
DE4334678A1 (de) 1995-04-13
TW291494B (no) 1996-11-21
PH32006A (no) 1999-06-02
PL313967A1 (en) 1996-08-05
HU9600946D0 (en) 1996-06-28
ES2134357T3 (es) 1999-10-01
FI961602A (fi) 1996-04-11
ATE180823T1 (de) 1999-06-15
EP0723574A1 (de) 1996-07-31
EP0723574B1 (de) 1999-06-02
DE59408367D1 (de) 1999-07-08
AU682540B2 (en) 1997-10-09
NO961434D0 (no) 1996-04-11
CN1141055A (zh) 1997-01-22
HUT74124A (en) 1996-11-28
CZ9601018A3 (cs) 2002-01-16
BR9407810A (pt) 1997-05-06
JPH09504314A (ja) 1997-04-28
WO1995010581A1 (de) 1995-04-20
KR100300774B1 (ko) 2001-11-22

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